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Prologue.

Ira Glass

From WBEZ Chicago, it's ThisAmericanLife, distributed by Public Radio International.

Woman

Good morning!

Men

Morning.

Woman

We want to thank everyone for coming out this morning. We're excited because it's an election time.

Men

Yeah!

Ira Glass

This rally was just last month, black elected officials from Chicago's West Side two days before the primary election there. What the rally was about, and what they were asking God to bless, was kind of unusual.

Reverand Randall

We pray now, Master, with this election time, that you bring clarity and understanding, and you'll bring victory back home to the ones that stand in the--

Ira Glass

Here's the victory that Reverend Randall is asking God to step in and help with. He wants God to help re-elect Derrick Smith to the Illinois State House for the 10th district. Smith had been arrested just five days before this for accepting a $7,000 bribe. He'd originally asked for $5,000. And then, he upped it to $7,000 and specified it had to be in cash, according to an FBI informant.

Allegedly, Smith was getting the money as payment for writing a letter of support for a daycare center to get a government grant. And this is the kind of case that when you hear the evidence, it doesn't seem to leave a lot of room for doubt. The exchange of money was recorded by the FBI. I read the 23 page FBI account of the case. Here's how it went down.

The informant counts out the money-- one, two, three, four, five, damn, stuck together, six, seven. Talk to you later. Smith says, you don't want me to give you yours now? I'm going to get you your two, man. He had promised the informant $2,000-- that's on tape also-- for bringing in the bribe. And you may ask, how do certain Democratic officials view all of that evidence?

Robert Steele

Derrick Smith has not been proven guilty. He is continuing to run for office.

Ira Glass

This is Cook County Commissioner, Robert Steele.

Robert Steele

So let's support Derrick until any time he's taken into the court system and found that anything that happens at that time. Derrick is an innocent candidate that's running for office. We're supporting an innocent candidate who's running for office. Let's support Derrick Smith! Let's support Derrick Smith!

Ira Glass

This is the official line of the day from the Democrats. And they came out in force-- five state reps, two state senators, for alderman, various commissioners, the Illinois secretary of state. 20 of them are listed on the press release announcing this rally, headlined by somebody who is generally seen as a stand-up guy, well-liked, long-serving US Congressman Danny Davis.

Danny Davis

We know that our colleague is charged with criminal activity. But we also know that a charge is not a conviction.

Supporters

Mm-hm, that's right.

Danny Davis

But we also know that there are circumstances that concerns us.

Ira Glass

And right here is when you get to the reason for the show of force by Democrats that day. The other candidate in this Democratic primary was Tom Swiss, the former director of the Cook County Republican Party. He entered the Democratic Party in the primary, according to an email that became public, because he thought it was going to be easy to win, calling the residents of the district, quote, "low information voters." Davis said that running a Republican in the Democratic primary was just subterfuge.

Danny Davis

And we want to make sure that we don't elect a wolf--

Supporters

That's right.

Danny Davis

--in sheep's clothing.

[CHEERS]

Supporters

That's right, that's right.

Danny Davis

That we don't elect a wolf in sheep's clothing. Should ultimately the judicial process determine that Representative Smith cannot serve, then there would be the opportunity to make sure that a Democrat--

Supporters

That's right.

Danny Davis

--that a Democrat--

Supporters

Say that again!

Danny Davis

--is elected to that position. And that's why we're here this morning. Support Derrick Smith, State Representative.

[CHEERS]

Supporters

Derrick, Derrick, Derrick! No deceit, no deceit, no deceit!

Ira Glass

I bring all this up because this week on our radio show, we have a bunch of stories in which people did something bad, like, you know, endorsing somebody who just accepted a bribe on tape just days before. And they knew it was bad. But it wasn't clear just how bad. After all, like Danny Davis, they had their reasons. And in putting together today's show, we got talking amongst ourselves about how bad actually counts as bad. Basically, we were talking about levels of sin and how to rate the different levels of sin. And once you get into that game, you really need to turn to a professional.

Father Torres

I'm a Franciscan priest, like a missionary priest, Father Agustino Torres.

Ira Glass

Father Torres works with low income people, especially young people in Paterson, New Jersey, and very generously agreed to run us through the Catholic notions of serious and less serious sins. Or, the old Catholic term for it, mortal versus venial sins.

Father Torres

A venial sin-- "venial" comes from the Latin word venia, which means basically to pardon, pardonable, something small. A mortal sin is something serious. The word "mortal" means something that kills. The three criteria for a mortal sin is it's serious, I know it's serious, and with all my faculties, I do it anyway. It's serious, I know it's serious, and I do it anyway.

Ira Glass

Mortal sins, unrepented for, send you to hell when you die. Getting right with God again to avoid that can take a long time and real personal change. Venial sins are so small that they're forgiven simply if you show up for mass. So under this scheme, a white lie, obviously a venial sin. Murder or adultery, mortal sins. The Ten Commandments, often but not necessarily mortal sins. Like for example, the commandment on taking the Lord's name in vain.

Father Torres

So John Doe is commuting back to New Jersey. He crosses two bridges, the Triborough and the George Washington Bridge. He's in two hours of traffic. And then, he gets home finally after driving home. And his son runs over him with his bike on his foot. And he uses the Lord's name in vain. Is that a mortal sin? That's grave matter. It's serious. But if you were to bring me that situation, I would say probably not.

Ira Glass

What you're saying is context counts?

Father Torres

It does count. But it doesn't necessarily change what you did.

Ira Glass

That's also true of intention. Your intentions count. So when Father Torres hears confession, which he does for eight hours a week or more, he asks people what happened, what their intentions were, what the circumstances were, and figures out from that the seriousness of the sin.

Father Torres

We sometimes claim ignorance. And that's a place where people say, well, I didn't know. Like, well, you did. If you had an inkling that it was wrong, then you knew. And we have something called a conscience. And a principle that we use is you never go against an uncertain conscience. So if you have a doubt, if this may not be totally right, well, that's your conscience saying don't do it.

Ira Glass

Hm. Oh, that's interesting. I've never heard that.

Father Torres

It's bread and butter right there.

Ira Glass

That's how you make your living, right there.

Father Torres

No, no, but that's a concept I use often. And this conversation that we're having, I've had a thousand times.

Ira Glass

So rule of thumb-- if you find yourself wondering if something you did was right or wrong, it's probably wrong. Well, today on our program, we have stories of three people who pretty much know what they are choosing is wrong. They don't even wonder. They know it. But they don't think it's that wrong. They make excuses. They dig themselves in deeper. In short, they act like you, and me, and everyone who has ever lived. Witness, 77% of Illinois 10th District who voted Derrick Smith another term. Stay with us.

Act One. The Postcard Always Rings Twice.

Ira Glass

Act 1, The Postcard Always Rings Twice. So a venial sin, a small sin just isn't that big of a deal, right? But turns out, if you keep committing the same venial sin over and over, if you pilot on, if you escalate, if you become-- this is in the words of one priest who we talked to this week-- callous of the heart, a venial sin can turn into a mortal sin through sheer volume. That is, a not terribly serious offense can become a very serious one, which is more or less what happens in this next story from Alex Blumberg.

Alex Blumberg

Let's start things off by introducing our sinner.

Jeff Smith

My name is Jeff Smith. I'm from St. Louis, Missouri. I was an educator there. I worked in the St. Louis City Schools. And then, I ran for Congress. I lost narrowly. Then, I served in the Missouri State Senate for three years. And then, I spent last year in federal prison.

Alex Blumberg

Now, Jeff Smith will be the first to tell you the sin that landed him in federal prison was hardly the worst sin of his life. In fact, among the myriad sins you'll hear about in this story-- sins involving drug dealing, lying to federal agents, attempted murder-- that original sin, the one that landed him in prison, might not even deserve the title of sin at all. But I'm getting ahead of myself.

The story begins in 2003 and starts with, of all people, former Congressman Dick Gephardt, from Missouri's third district.

Jeff Smith

Dick Gebhardt, who'd represented the third district for 28 years, had run for president twice unsuccessfully, but was the leader of the house Democrats, decided to retire.

Alex Blumberg

And Jeff Smith decided to run for his seat. Now, let me just list the ways this was an utterly foolish decision. Jeff Smith was a part-time political science professor who'd never held any elective office-- not councilman, not dog catcher, nothing. His opponent in the Democratic primary, on the other hand, Russ Carnahan came from one of the most prominent political families in the state. As the Bushes are to Texas, the Kennedys are to Massachusetts, the Carnahans are to Missouri.

Russ's dad, Mel, was the governor of Missouri. He died in a plane crash in 2000 as he was running for Senate. Russ's grandfather also served in politics, a seven-term congressman from Missouri. Russ's mom, Jean, served briefly as a US Senator from Missouri. And his sister, Robin, is Missouri's Secretary of State.

Add to this that Jeff Smith was 29 years old, 5' 6", 120 pounds, with a funny voice and a penchant for baggy, hand-me-down suits. He came across less like a candidate for Congress and more like a well-spoken teenager running for class president. In fact, his own family thought his candidacy was ridiculous.

Jeff Smith

Well, actually, I went to dinner at my family's house. And I told my parents and my brother that I planned to run for Congress. And they laughed at me. My brother was imitating Beavis and Butthead. "Uh, if you win, would you, like, get Secret Service and stuff?" You know, just moronic things like that. My mom said, "What are you running away from? Why don't you just settle down and have a normal life? This is the most absurd thing I've ever heard."

My grandma, she was 95 at the time. One of her bridge partners received my first solicitation letter. And her bridge partner came to the bridge game and said, "Hey, can I write your grandson a check, you know? Where do I send it?" And my grandma said, "If I were you, I'd save your money."

Alex Blumberg

Still, there was a method to Jeff's madness. There were 10 candidates competing in the primary. And Jeff figured, as one of the most outspoken and liberal candidates in the pack, he'd be able to stand out, generate just enough votes to eke out a win over the man everyone considered the front-runner, Russ Carnahan. Jeff had been a very popular part-time professor, and a lot of his former students began to volunteer for his campaign.

This volunteer force of 20-somethings grew steadily into one of the biggest and most well-organized ground games in the primary. And Jeff Smith had another valuable asset-- his best friend, Steve Brown.

Steve Brown

I guess that you would say I was chairman of the kitchen cabinet, so to speak.

Alex Blumberg

Steve Brown and Jeff Smith had first met during Steve's failed bid for the state legislature in 2001. Jeff had been Steve's campaign manager. And during that campaign, they discovered they were each other's political soul mates. They had the same principles, the same beliefs, the same obsessive interests in the details of political strategy. They would spend hours a night discussing the nuances of messaging, how best to implement a get out the vote campaign, whose political fortunes were rising and whose were falling.

And when Jeff told Steve he was running forgot Gephardt's seat, Steve-- unlike Jeff's own family-- was immediately behind him. Steve was not an official member of Jeff's campaign. He had no formal role. But his unofficial role was big because Steve, unlike Jeff, came from a wealthy and politically connected family.

Steve Brown

My specific goal was attempting to help introduce him to people that would help him raise money. My family had spent a lot of time in Democratic politics in the state and doing other charitable work, as well. And I had access to people that could write him checks. And my job was to put him in front of those people. If I had a specific role, that's what I would try to do.

Alex Blumberg

One other thing that must be said-- Jeff Smith was a very gifted campaigner. On the trail, he was funny, sincere, great in front of a crowd whether that crowd was a bunch of liberal college kids at a coffee shop in St. Louis or group of wealthy donors in the suburbs. And over the course of the race, Jeff's campaign steadily gained momentum, attracted more volunteers, more money, and professional campaign consultants.

One sure sign that your campaign is doing better-- more and more professional political types come forward to try and sell you their services. And it was an encounter with one of these types that sent Jeff down his windy, improbable path to prison. Here's Jeff.

Jeff Smith

We were approached by a man named Skip Ohlsen who billed himself as a practitioner of political dark arts. He also claimed to be very close to the governor. Apparently he had spent the night in the governor's mansion, had raised money for the governor and lieutenant governor.

Alex Blumberg

Skip presented himself as a seasoned media consultant who wasn't afraid to get his hands dirty. And Jeff said, no thanks. But as the campaign heated up and entered its final months, it became clear it wasn't going to be enough for Jeff just to plant more yard signs than his opponent. He needed to attack Carnahan. And Jeff had just the issue he wanted to hit him with.

Jeff Smith

When Carnahan had served in the state legislature, his attendance record was dismal. He had missed more votes and more days of work than almost any of the state legislators and had passed no meaningful legislation.

Alex Blumberg

So when Ohlsen came back to Jeff's campaign to offer his services again, the campaign took him up on it. Two of Jeff's staff members met with Ohlsen and shared Carnahan's attendance data with him. Ohlsen was going to send out direct mailers to voters in the district highlighting this attendance record. The problem was Ohlsen was going to do this as an independent expenditure.

For those not schooled in the intricacies of election law, an independent expenditure is money that could be spent on ads, mailers, whatever, that is not subject to campaign finance limits. The Swift Boat ads from 2004 targeting John Kerry, those were independent expenditures. The catch is there's supposed to be no coordination between the group putting together the independent expenditure and the campaign.

So for members of Jeff's staff to be coordinating with Skip Ohlsen on these mailers was illegal, even if the coordination involved nothing more than supplying him with publicly available data on Carnahan's attendance and voting record. Now, Jeff knew all this. But he gave it the go ahead anyway.

Jeff Smith

My two staff people came back to me at headquarters. They said, "This guy wants to do this independent expenditure." And instead of saying, "I don't want you to meet with him," I said, "Hey, I don't want to know any of the details," which was essentially giving tacit permission for them to go and give him that information.

Alex Blumberg

This was Jeff's first sin. The minute he knew that his staff people were coordinating to produce an independent expenditure, he was complicit in this illegal act. And he knew that. But as sins go, especially political sins, it didn't seem that bad-- the political equivalent of jaywalking. Jeff figured, this is the sort of thing that happens all the time.

The campaign put Ohlsen in touch with Steve Brown, who found somebody to pay him. That part was legal, by the way. Remember, Steve Brown was not an official member of Jeff's campaign. And then, everyone went back about their business. Here's Jeff Smith.

Jeff Smith

Over the course of the whole campaign, I didn't think about it for more than 15 minutes probably. It was just one more decision in a long string of decisions that you make every day. You make thousands of decisions. And my focus was 600 volunteers, making sure that I had 20 full-time interns who were all college kids or high school kids.

And I had a great field director. I wanted to make sure they were all knocking on doors. I wanted to make-- I needed to raise the money to make sure that we could get up on black radio, that we could do TV ads, that we could fill out our direct mail program. I mean, really, I doubted that it would ever happen because I didn't view Skip Ohlsen as being a credible person. And I doubted that he'd ever follow through with it.

Alex Blumberg

For weeks and weeks, it seemed Jeff was right to doubt. But then, in the final days of the campaign, Skip sent out the mailers, postcards to addresses all over the district highlighting Carnahan's attendance record. Jeff didn't even know the mailers had gone out until Jeff's press secretary go a hold of one.

Jeff Smith

He shows it to me, and it was this amateurish thing. I mean, it looked like a seventh grader did it at the last minute after procrastinating for three weeks on his end of the semester project. It was not well done. And we immediately notice that it lacked a disclaimer.

Alex Blumberg

That is, that little thing at the end of all political ads, "Paid for by Citizens for Fairness," or "Taxpayers for Justice." See, the way an independent expenditure is supposed to work, a separate entity is formed and registered with the Federal Elections Committee, the body in charge of federal election law. The name of that entity is supposed to be present on all the political materials it sends out. Here's Steve Brown.

Steve Brown

And for whatever reason, I certainly didn't know that he was going to do it, he put on there sort of a bogus disclaimer saying, "Paid for by rustycarnahan.org," OK?

Alex Blumberg

Uh-huh.

Steve Brown

I don't know why he did it. If he had put the regular thing on there and they had found out that I was involved, it wouldn't have bothered me in the slightest. We didn't want him to do that. He did that.

Alex Blumberg

And what was it supposed to say? paid for by-- what was it supposed to say?

Steve Brown

Voters for Truth which was just an entity that he had created to conduct--

Alex Blumberg

Right.

Steve Brown

--to conduct business, called Voters--

Alex Blumberg

That was the entity that had all the t's crossed and the i's dotted, and all that sort of stuff? It was legal, basically?

Steve Brown

Yes. It was a committee, or it was an independent expenditure set up properly.

Alex Blumberg

Putting a disclaimer on a political mailing is a pretty basic thing. To this day, it's unclear why Skip Ohlsen didn't do it. But since he hadn't, there were now 25,000 disclaimerless postcards out there. And the amount of damage that that one omission opened the door to is truly staggering.

What happened in this case is that Russ Carnahan also noticed that the mailer lacked a disclaimer. He noticed Jeff Smith holding press conferences raising the same exact points about his attendance record as the mailer did. And he probably noticed as well that when you clicked on rustycarnahan.org, you came to a page with an illustration of a barefooted person on a beach napping in a hammock.

And so with roughly a week before the election, he filed a formal complaint with the FEC saying essentially, here's this illegal mailer. I think Jeff Smith is behind it. Investigate, please.

And then, about a week later, election night came. The race was much closer than anyone thought it would be. At several points during the night, it looked like Jeff might actually win. But in the end, he was edged out by Russ Carnahan-- final margin of victory, less than 2,000 votes. A day or two later, Jeff met with Russ Carnahan in the obligatory water under the bridge post-primary fence-mending session.

Jeff Smith

I said, "Hey, congratulations, you won. I'm happy to help you now in the general election. I want to make sure a Democrat holds this seat. I'll endorse you. I can do it publicly. I can do a press release, however you want. I'll raise money for you. I'll knock on doors for you. I'll ask my volunteers to knock on doors for you." He said, "Great."

I said, "I do have one request. I'd love it if you'd drop that FEC complaint. And my support will not hinge on your decision. I'll still be happy to do those things. But as a gesture of goodwill, I'd appreciate it if you'd drop the complaint." And he looked at his brother. And his brother said, "You know, I'm sorry, but I'm afraid the missile's already left the silo."

Alex Blumberg

Some time later, Jeff received a copy of the FEC complaint in the mail. He showed it to his lawyer, and she prepared an affidavit for him to sign, an affidavit claiming Jeff Smith had no knowledge of who was behind the postcard. This, of course, was not true. But Jeff signed it anyway.

Now, this was a big step. Making a false statement on an affidavit in response to a federal investigation-- that took him out of wrist slap territory and into potential prison territory. But Jeff didn't really appreciate the magnitude of this much larger crime because it was still linked, in his mind, to that smaller, original one, that technically illegal coordination over a postcard.

And plus, the campaign was over. He'd lost. He knew he'd never do anything like this again. It had left a bad taste in his mouth the first time. He was worried about implicating his staff people who'd met with Skip Ohlsen. And he was already in debt from his race and worried about paying a potential fine himself.

Jeff Smith

And so for a variety of reasons-- none of which I say to excuse my terrible mistake-- I just went ahead and signed it. I just figured, I did an instant calculation in my head. I know there's hundreds if not thousands of these situations across the country every election cycle. There's always accusations of coordination.

Most of the time, they're probably right. But it's probably not provable. And I will assume this complaint will just fall into that huge stack that they'll look into, not be able to figure anything out definitively, and that'll be that.

Alex Blumberg

And in fact, for two years, basically nothing happened with the FEC case. During that time, Jeff made another bid for elective office, this one successful, and got himself elected to the Missouri State Senate.

Jeff Smith

And then, about right after I got elected to the Missouri Senate, things heated up again. And Skip called my friend, Steve Brown, and said "They want to talk to me." And Steve called me and told me that. And he said, "They're going to talk to Skip. But don't worry. I'll take care of Skip."

Steve Brown

I talked to him and had a long conversation with him.

Alex Blumberg

Again, Steve Brown. He says he tried to convince Ohlsen not to say anything to the FEC.

Steve Brown

And I hung the carrot out there of working on future campaigns with me and Jeff and making some money if he were to sort of fall on his sword and have this investigation end with him.

Alex Blumberg

Uh-huh. And did you think that he was going to do that?

Steve Brown

I was not 100% confident that he was going to do that.

Alex Blumberg

Now, at this point, Steve Brown was an Assistant Attorney General for the state of Missouri. So he, of all people, knew that it was illegal to do what he was doing, to try and get Ohlsen to lie to the FEC. But he says he was thinking about it not like a lawyer, but a politician, the same way Jeff was.

That original infraction was so minor and technical, about a postcard, and there was a lot at stake now. he and Jeff both had exceeded everyone's expectations with that campaign. Their political fortunes were on the rise. Steve was worried that an FEC violation would damage all that. And he figured, who would ever find out about a private conversation like this anyway?

Plus, it's not like the FEC has a reputation for aggressively pursuing campaign finance violations. Many people consider it a bit of a joke as an enforcement agency. And for about a year after Ohlsen talked to the FEC, nothing happened. During that times, Steve Brown left his job in the Attorney General's office and also got himself elected to the state legislature on the House side.

So now, he and Jeff were going to be serving together. Things were going great. And then, in the winter of 2007, the FEC came out with its report saying they were dropping the case. Skip Ohlsen was just too unreliable a witness. Steve Brown recalls getting the news.

Steve Brown

Jeff called me up and said, "I've got a present for you. I've got to come by and show it to you." And he comes by and gives me a copy of the final report that sort of closes the matter. And I say to him, "Boy, I think we really dodged a bullet on this one." And at that particular point in time, I did think this was over.

Alex Blumberg

In fact, reading the report, it only reinforced the notion that the FEC wasn't much of an investigative body. They never even talked to Steve Brown, although he did see his name mentioned.

Steve Brown

A footnote in the investigation said, "Skip Ohlsen says Steve Brown helped provide the money for this effort." Something along the lines of, we doubt that this person even exists. We've been unable to locate him and doubt that he even exists. And at that particular time when the FEC wrote that, my name was on the ballot in Missouri. But be that as it may, they closed their investigation at that point.

Alex Blumberg

And that is the point where the matter would have died if not for one of the strangest and most random twists you could imagine. Late afternoon on a Wednesday in October, 2008, a 69-year-old attorney found a wicker basket next to his car, an Acura, in the parking garage of his office.

When he picked up the basket, it exploded, severely burning his hands and face. The police could find no motive. This man didn't seem like the type of guy who'd provoke an attempt on his life. Who was trying to kill him? They didn't find any suspects.

But they did discover that there was another Acura often parked in that same garage just a floor away. And this Acura belonged to a divorce attorney, a divorce attorney who happened to represent the estranged ex-wife of one, Skip Ohlsen, the practitioner of the political dark arts. Steve called Jeff with the news.

Jeff Smith

He called me one day right after session and told me that Skip Ohlsen was being investigated for a car bombing of Skip's ex-wife's divorce attorney. And we were just like, oh my god. And then, Steve told me that Skip actually was also being investigated for illegal weapons possession, and mortgage fraud, and bank fraud, and had also been convicted before of cocaine distribution, and domestic violence, domestic abuse, just a whole litany of things. And we had thought-- had a hunch-- that Skip was a little bit shady. But we, of course, had no idea of all of that.

Alex Blumberg

You didn't think that he was capable of murder?

Jeff Smith

No.

Alex Blumberg

Jeff worried, what if Skip tries to cut a plea deal by saying, "I have damaging information about two state lawmakers?" So he and Steve met to talk it over.

Jeff Smith

Well, Steve comes to my house and one of my former staffers from 2004, comes over. And we discuss how we're going to handle the situation. I say, "Hey, I'm already out there. I signed an affidavit, OK? Saying that I didn't know anything about this. So I'm just going to stick to that."

And Nick Adams, my first staff person in 2004, Nick said, "Hey, this is the word of one cocaine distributing, wife beating, convicted felon against the word of a state representative and lawyer-- Steve Brown-- and political science professor and state senator. Who are they going to believe?" And I agreed with that. And I said, "I think we should just stick to the story."

So Steve called me several times over the course of a couple months. And we met in person and discussed all of this frequently. And little did I know that that entire time he was wearing a wire.

Alex Blumberg

So that when you were meeting at your house, he was wearing a wire?

Jeff Smith Yes.

(SUBJECT) JEFF SMITH: Yes.

Alex Blumberg He

(INTERVIEWER) ALEX BLUMBERG: He had you on tape saying--

Jeff Smith

He had me on tape saying the following. I said something to the effect of, "Did I know that Skip was going to do that postcard? No, I didn't know. But I guess you could say that I had a pretty good hunch." So I say something to that effect, something pretty close to that on tape.

Alex Blumberg

So why, you might be wondering, was Steve Brown taping this conversation? Well it turns out that three years earlier, when Steve had had that conversation with Skip Ohlsen, the one where he tried to keep him from testifying to the FEC, that conversation in which he'd promised material rewards if Ohlsen lied to federal investigators? During that conversation, Skip Ohlsen had been wearing a wire on Steve.

When the feds went to investigate Ohlsen for his various illegal activities, they found this recording along with a stack of other ones. It appeared surreptitiously recording people with whom he was conducting business was a bit of a habit of Skip Ohlsen's. Some time after discovering these recordings, FBI agents approached Steve as he was leaving his house. Steve contacted his lawyer. His lawyer found out about the recordings. And he came back with some very bad news for Steve.

Steve Brown

He said, "You are in very big trouble. There's going to be a felony conviction. You're going to lose your law license. You're going to lose your political career. The job now is to try to keep you out of jail." So that came down instantaneously.

Alex Blumberg

Steve says that right at that moment, his attorney laid out the strategy for keeping Steve out of jail.

Steve Brown

And of course, that includes assisting the federal government in building their case against Jeff. Here I was-- I mean, Jeff and I over the years would talk for hours into the middle of the night, on the phone constantly. And here I was going to have one of those conversations with Jeff knowing that the purpose was to get him to say things to incriminate himself that would ultimately get him prosecuted.

Alex Blumberg

And what are your thoughts? What were you thinking at that time?

Steve Brown

It's really very hard to put it into words. It was a dark, dark day. I mean, this is a crappy situation. And if Jeff were sitting across from me right now, I'd apologize to him for doing it. But it was clearly what was going to happen. I had lost my life for Jeff. I lost my political career. I lost my law license. I lost a reputation. And I lost all that in an attempt to help Jeff. And that was as far as I was prepared to go.

To be honest, sorry, Jeff, you're a good guy. I had hoped and planned to do great things with you. But I'm not risking-- I'm not taking away from my two children and my wife for you or anybody else. And so thinking about them is what really got me thinking what I needed to do keep myself out of jail.

Alex Blumberg

It turns out being a great cooperating witness and someone's closest friend, there's a lot of overlap. Steve and Jeff would talk about Skip Ohlsen's investigation. And Steve would ask Jeff, what are you going to do if they come to your house?

Jeff Smith

I say at one point on the tape, "I'm going to be 90% honest with them." So right there, there's a count of obstruction of justice.

Alex Blumberg

Right.

In the end, Jeff was charged with nine counts. On the day the feds came to his door and charged him, he went to his lawyer's office.

Jeff Smith

Then, she called the US Attorney's Office. And she came back 10 minutes later and sat me down with another attorney and said, "Your best friend has been wearing a wire for the last couple months. And you're probably going to go to prison."

So I drove to my parents' house. I called them, told them I needed to come over and talk to them. It's only about five minutes away. But it was probably the longest five minutes in my life. And I told them, "Hey, guys, listen, I made a big mistake in my first campaign and immediately afterwards. And I'm probably going to go to prison. And let me explain what I did."

And my mom's response was-- I probably could have predicted-- she said, "I knew this was going to happen. I told you that politics was dirty. I told you not to get mixed up in this. I told you that you shouldn't have ever run for office." Maybe not what I needed to hear right at that moment. But I understood where she was coming from because she had been the loudest voice from the start telling me it was the stupidest idea she'd ever heard for me to run for office.

Alex Blumberg

Jeff was sent to federal prison in Kentucky to serve his one year sentence. He stood out in many ways there-- 5' 6", 120 pounds, white, Ph.D. Plus, he was one of the few people in the facility not serving a drug sentence. In fact, his fellow inmates had a hard time figuring out, wait, how exactly did you end up here?

Jeff Smith

They thought I embezzled millions. They're like, "Man, you pulled Blago [BLEEP]," you know? Because the Blagojevich stuff was happening. I'm like, "I didn't get any." They're like, "Then why'd you end up here?" I'm like, "It wasn't about money." They're like, "Man!" And they'd all just be like, "What the [BLEEP] is wrong with you? End up in prison, you didn't even get no money?"

They thought I was really stupid. I mean, they thought I was really stupid. They're like, I'm in prison for a postcard?

Alex Blumberg

During his time in prison, Jeff had a lot of time to think about that postcard-- his own mistakes in allowing it to happen, but also the utterly improbable chain of coincidences that allowed that postcard to come back and get him. If Skip Ohlsen had just put the proper disclaimer on the postcard, for starters, identifying the organization that he had in fact gone to the trouble to properly set up. Or, if Skip Ohlsen hadn't tried to car bomb his ex-wife's divorce attorney. Or, if he hadn't had a penchant for surreptitiously recording conversations with business partners. Take out any one of those things, and Jeff Smith wouldn't have been sitting in his prison cell.

And then, there was Steve Brown, his best friend who had worn the wire. It's a hard thing to get over. In the beginning, Jeff says, he had a lot of bitterness towards Steve. But early on, Jeff found a mentor at the prison, a former drug dealer serving a multi-year sentence, nicknamed KY. KY overheard Jeff talking about Steve Brown to some other inmates.

Jeff Smith

KY soon thereafter took me aside because somebody had asked me in a group setting-- kind of jokingly asked me, "Hey, man, let me get after your boy. I'll have someone get after your boy." Basically joking around, saying, hey, we can have someone go do something to Steve Brown. And I was sort of humoring him, like, oh, what are they going to do to him?

And KY took me aside and said, "Man, you gotta put that dude outta your mind. Don't even think about him." He's like, "My brother-in-law told and got me here." He's like, "My first year, that's all I could think about, what I was going to that [BLEEP] when I got out." And he's like, "You know, you can't do time like that. You see these other dudes, that all they're doing is worrying about the dude who told on them and what they're going to do to him when they get out and all this?" He's like, "You just can't get through your time. You gotta focus on positive stuff."

Alex Blumberg

What happens if you don't? What happens?

Jeff Smith

It's too much. I mean, you just eat yourself up. You go back in your cell at night. And you're just sitting there thinking about it. You can't do that. You can't get through-- I mean, I only had this little bit of time compared to those guys. Most of those guys had 10, 15 years. It's just a miserable experience. It's just miserable being away from the people you love. And prison sucks.

Alex Blumberg

And it sucked even more precisely for the reason that prison is supposed to suck. He had time to think about what he had done. And there was a lot to jog his memory in the transcripts of the secret recordings Steve Brown made. At a certain point during the several months in which Steve Brown is recording, the Fed's approach Jeff and question him. And Jeff lies to them about what he knows about Skip Ohlsen.

Later in conversation with Steve Brown, he goes back and forth about what he should have done. At one point, he says, quote, "Do you think I made a huge mistake today telling them I didn't know who did the mailer? If I called them back, would that change things?" But then later in the same conversation, he tells Steve, "If the feds come and interview you," quote, "can you just shade it at all?"

During another moment, he appeals to Steve to blame the whole thing on one of his staffers who'd coordinated with Skip Ohlsen who'd since died. Another time, he tells Steve, quote, "I hate to say this, the only way they can get me is if you or Nick--" another former staff member-- "says something." And when Steve refers on tape to the conversation he had with Skip Ohlsen where he tried to get him to lie to the FEC, Jeff says, quote, "You can't tell them that." And, quote, "You'd be an utter fool to tell them you crossed over the line."

To Steve Brown, it felt like he was the one being betrayed by his best friend.

Steve Brown

There were times when it was clear to Jeff that the heat was on, OK? The FBI had visited him. He now knew that extreme consequences were attaching to our actions, OK? And the only thing that came to his mind during that time was to continue to tell me to lie and put myself at risk. I mean, what if he had said, "Steve, I love you. You're my best friend. I can't ask you to do this anymore. I'm gonna go talk to these people and see what I can get done." He never said that. All he could tell me to do was lie.

Jeff Smith

I understand why he would feel betrayed by that.

Alex Blumberg

Really?

Jeff Smith

Yeah. Yeah, I mean, it was not a good moment for me, you know?

Alex Blumberg

Why didn't you tell him that, though, do you think? It's to protect yourself, basically, like talk to the feds if you need to, et cetera.

Jeff Smith

Alex, man, if you talked to 1,000 people in the world that were in a situation at all similar to what I was in and you asked 1,000 of them, "Tell me the truth, why didn't you go to one of the only other people that could've gotten you and go to the feds and just tell them whatever it was?" I don't think you're going to find many of those 1,000 that will honestly tell you, "Yeah, I should have gone to tell them, hey, go to the feds and tell them anything and everything that happened."

I just don't think you're going to see that much. I mean, you feel like you're hunted pray when the feds come knocking on your door at 6:30 in the morning. And you're right. Of course I should have been like, "Steve, you do what you need to do." But I felt sort of like we had made this agreement long ago. And for any one of us to go soft now was to get us all into trouble.

I mean, the way we talk about it, it's like there were six dead bodies in vacant houses somewhere. I mean, it's just so silly. I just didn't feel that compelled to say to Steve at that point, "We need to let them know everything."

Alex Blumberg

In the years since Jeff was released from prison, he's managed to put his life together. He got married, had a kid, landed a job teaching public policy at the New School in New York City. He's written a book, although he still needs a publisher. Steve Brown has found it a bit more difficult. He still has his wife and his children, but he can't practice law anymore, can't do politics, and he's yet to successfully transition to a new career. It's tough to do in your mid-forties. They both say they've moved on from this. Neither wishes the other ill. But the two men haven't spoken since the day Jeff found out that Steve was wearing a wire. Betrayal-- it's a hard sin to forgive.

Ira Glass

Alex Blumberg is a producer for our show often heard on the PlanetMoney podcast. Coming up, the intoxicating effect of guns, spying, and the Teenage Mutant Ninja Turtles. That's in a minute from Chicago Public Radio and Public Radio International when our program continues.

It's ThisAmericanLife. I'm Ira Glass. Each week on our show, of course, we choose a theme and bring you different kinds of stories on that theme. Today's program, Mortal vs. Venial. We have stories of people trying to figure out just how bad they are. How bad is bad?

Act Two. The Disenchanted Forest.

Ira Glass

We've arrived at act two of our program-- Act Two, The Disenchanted Forest. So lying is a sin, right? And lying to ourselves is also wrong. But what about the lies that we all collectively believe because they make us feel better? They give us hope? How bad are those? Mortal, venial, less than venial? Jonathan Goldstein has this story about confronting the truth.

[GAVEL BANGS]

Jonathan Goldstein

Honorable animals of the forest council, Secretary Otter and Chairman Skunk, I'm sorry, but I must interrupt. I know that time is of the essence. So I will keep my remarks brief. I stand before you not an arrogant hare, nor a flashy hare as some of you would have it, but merely a hare who cares about this forest and all of its creatures.

I've not come here to cast dispersions on the tortoise. This is not a time for partisanship. Whether you be a hare man or a tortoise man, we must all work together. But to save the forest from its impending doom, it's important you know the truth about the race known as Tortoise versus Hare.

Look, I know how this makes me look. The hare is a poor loser, you say. The hare has a problem with tortoises. Well, I'm going to stop you right there. Let the record show that I have nothing against turtles of any kind. The snapping turtle is godfather to 27 of my kids, for crying out loud.

But if you think there is any chance that tortoise beat me fair and square, you are deluding yourselves. Tortoises don't have a reputation for being slow. They are slow. Everyone knows this. It's not a question. It's not debatable. It just is.

So imagine my surprise when, one morning, I wake up to discover the entire forest is talking about how I challenged the tortoise to a race. Think about it. Why would a hare challenge a tortoise to a race? It doesn't make any sense. What would it prove? If I win, I'm an [BLEEP]. If I lose, I'm an embarrassment to my species.

Oh, how I was vilified after that race. In the picture they ran on the cover of TheForestPost, I'm pulling my whiskers out, stomping on my top hat and yelling at a judging official. There I was, the arrogant buck-toothed hare with the fabulous libido that everyone loves to hate finally receiving his comeuppance. And the lies that were told about the race itself-- why would I stop just shy of the finish line and eat a large turkey dinner with all of the trimmings? Or why would I pull out a beach chair and take a sun tanning break? First of all, I burn easily. And second, what am I, an idiot?

In the days after the race when I put forth my multiple tortoises in multiple forest nooks theory, I was labeled a paranoid, a conspiracy nut, not to mention a specie-ist for suggesting that tortoises all look the same. But I knew then as I know now that there was a network of them, tortoises, all working in cahoots, stationed behind trees, hiding in briar patches all along the racing route. Nonetheless, the tortoise was awarded the title of fastest in the forest. And I'd no choice but to shake his wrinkled, little, green hand and congratulate him.

But dear fellow forest dwellers, back to the business at hand of this emergency meeting. As Smokey Bear alerted us this morning, the forest is burning. Time is of the essence.

With all due respect to the authority of this council, sending the tortoise as messenger to alert the creatures of these woods that there's a fire raging and they must run for their lives? Not the best choice in the world. The tortoise left three hours ago. But if you rise up onto your toes, you can still see him creeping along down there at the bottom of the hill.

So he cheated. And normally, I would let this go. Who among us has not cheated at one time or another? Opossum has cheated at checkers. Fox has cheated on his taxes. And I'm the first to admit that because of my own arrogance I've cheated myself out of your friendship. And I've also cheated with some of your wives.

But the point is we can no longer let this tortoise charade go on. If we don't do something now, lives will be lost. So just give me the OK to get running and as soon as I pick up my top hat at the blockers, fill my jogging pipe with tobacco, eat a light dinner of sprouts and Tam Tam crackers and get my retainer inserted, I'll be on my way. All in favor, say "aye." For the love of this forest and all that is good, please say "aye."

Ira Glass

Jonathan Goldstein. His story about the tortoise and the hare is itself based on a retelling of the Aesop's fable by the 18th Baron of Dunsany, Edward Punkett. Jonathan's the host of the CBC radio show and podcast, WireTap, which you can hear on many public radio stations and you can get from the iTunes Store, where a version of this story first ran.

Act Three. The Geeks Come Out at Night.

Ira Glass

Act Three, The Geeks Come Out at Night. So because the line between a mortal and a venial sin can be kind of hazy, sometimes the only way to know exactly where the line is just to test it. And that is particularly true when you're little. Where your parents set the line, well, sometimes you need to figure out if you agree with your parents on where that line is. Jonathan Menjivar tells this story about a time that he tested that line.

Jonathan Menjivar

When I was in junior high, I spent a lot of time with this kid, Tommy. That's not his real name. We went to the same school. But we ran in different circles. And then, we started hanging out in Boy Scouts. And Tommy scared the hell out of me.

I came from a strict household-- not violent strict, but "Come here-- take a close look at these cabinets and tell me you don't see the dust" kind of strict. So I was obedient and stuck to the rules. Tommy was like my real life after school special. He did all the stupid things I knew I had to avoid if I didn't want to get in trouble or end up hurt.

We all had BMX bikes, but Tommy was the only one who would try crazy jumps. He lifted weights and got bad grades. Tommy's house was the first place I saw porn and a gun.

We were in his parents' bedroom. And he pulled his dad's pistol out of a nightstand drawer and tried to show me how to load it. I left the room before the next scene of this very obvious plot could unfold.

The miracle of Tommy was that he got away with things. He didn't get caught and he didn't get hurt. At least, not that bad.

When I was with him, the world seemed bigger. He was always blowing right past boundaries that I didn't even know how to approach. One day, Tommy told me he had a huge crush on a neighbor who lived across the street from him, this married woman who was pretty in a metal video kind of way. She was blonde with that super short haircut Demi Moore had in Ghost, and Tommy said he'd seen her naked.

He told me that sometimes at night, he'd get all dressed up in black clothes and sneak out of his house so he could look in her bathroom window. He said he'd seen her come out of the shower. To me, the whole thing seemed more frightening than sexy-- and wrong. Tommy didn't seem to have that problem.

So Tommy came to my house for a sleepover. I think we'd stopped using that word, but that's what it was. I was used to putting on my pajamas at 6:00 and settling in for the night.

Tommy showed up with a duffel bag and came into my room, clearly prepared for something else. He shut my bedroom door, opened the bag, and pulled out all these homemade weapons he'd made in his dad's garage. There were several foot-long swords made from pieces of sheet metal with little wood handles and a weapon called a sai, like the one the Teenage Ninja Turtle Raphael used. God, I loved Raphael.

Anyhow, Tommy took all the weapons and stuffed them in between my mattress and box spring and pretended like it was all totally normal-- which I did, too. Then, we did your standard sleepover stuff, baked some pizza or whatever. And I fell asleep watching SaturdayNight Live.

A little after midnight, Tommy woke me up. He said it was time for night maneuvers. Night maneuvers was this game Tommy and a friend had made up where they'd basically taken all the things we were into-- role playing games, and Atari, and ninjas-- and they tried to make them real. They would dress up at night in black and run these little missions around the neighborhood, sneaking around, and sometimes going into people's yards to see what could be seen. That was night maneuvers.

We snuck out my bedroom window and ran from shadow to shadow on my street, hiding behind cars and bushes so no one would spot us. We were both wearing black. Tommy was the one wearing a backpack with swords in it. My heart was racing. But it wasn't actually fun. We hadn't gone far. We were still on my street, just a few houses away. And I was sure we'd get caught.

Each time we went for it, we had to run through these big, bright spots from the street lights and then crouch down again. Every time, I would hesitate and fumble thinking, this is bad, this is bad, this is bad! I'm gonna get caught, I'm gonna get caught, I'm gonna get caught! It never got easier. But Tommy did it with grace, like this was his Olympic sport.

We went down the street, snuck around in the backyard of a friend of mine, and then jumped a fence and ended up near these railroad tracks where there weren't any streetlights. Finally, a place where no one was going to see us. We were safe.

And for the first time, I felt just how incredible what we were doing really was. Here at night, letting my eyes adjust to the dark, looking up and seeing whatever little stars were there, was completely freeing in a way I didn't even know was possible. I don't think there's anything I could do right now that would give me the sense of confidence and possibility that I felt then, being outside like that with no one to watch over me. I thought that that's what it must feel like to be a grown up. The air felt good in my lungs, the night wide open.

I watched Tommy jump into a couple yards and peer through sliding glass doors. From where I stood, safe on the other side of a cinder block wall, Tommy didn't seem to have superhuman calm or ninja moves anymore. He was just a dumbass kid, out at night, looking for things to get away with-- same as me. I thought he'd probably never even seen his neighbor naked.

We started heading back to my house. And then, something happened that sobered me up. It separated the Tommys from the Jonathans. We got near a streetlight and decided to duck behind a car. From the driveway, we could see a man watching TV in his living room. It wasn't long before the man took his eyes off the TV and noticed us.

Tommy yelled at me to run. But, you know, I'm chicken. So I just stood there while the man caught us and screamed at us, saying whatever we'd done to his car, we were going to pay for it. I was sure we'd pay heavily. Then, the man looked into my eyes and said the most frightening words I'd ever heard-- "I know who your parents are." He let me stew in the fear for a while. And then, he let us go.

We ran back to my house and snuck into my bedroom through the windows. It was like everything we'd just done was rewound back onto the tape, never to be heard again. I crawled into bed and felt my heart was try to escape my chest for a good half hour. Tommy fell asleep right away.

That night was the first and last time I tried night maneuvers-- the last time I tried anything, really. I never TPed anyone's house. I didn't drink until I was in college. I wasn't even tempted with something a little bit bad, really bad. I didn't care anymore. Either way, I knew I didn't have the stomach for it. And I was totally OK with that.

Our website, where you can get tickets to our May 10 cinema event, coming up soon-- if you have heard about me talking about this already ad infinitum, you know that we are doing our show on stage. We're beaming it into movie theaters everywhere. We've added David Sedaris to the all-star lineup. David Sedaris now joins Mike Birbiglia, David Rakoff, Tig Nataro, Snap Judgments, Glynn Washington, and others. This, I say in all sincerity, is the most ambitious live event we've ever done filled with things designed for you to see-- animation, dancing. Tickets are going fast. It's one night only, May 10. Find a movie theater near you at thisamericanlife.org.

ThisAmericanLife is distributed by Public Radio International. WBEZ management oversight for our program by our boss, Mr. Torey Malatia, who sees all the long hours that we put in here on the radio show and asks me all the time,

Jeff Smith

What are you running away from? Why don't you just settle down and have a normal life?